WO2014180215A1 - Composition agrochimique et son procédé de préparation et d'utilisation - Google Patents

Composition agrochimique et son procédé de préparation et d'utilisation Download PDF

Info

Publication number
WO2014180215A1
WO2014180215A1 PCT/CN2014/075131 CN2014075131W WO2014180215A1 WO 2014180215 A1 WO2014180215 A1 WO 2014180215A1 CN 2014075131 W CN2014075131 W CN 2014075131W WO 2014180215 A1 WO2014180215 A1 WO 2014180215A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
agrochemical composition
spp
group
general formula
Prior art date
Application number
PCT/CN2014/075131
Other languages
English (en)
Inventor
James Timothy Bristow
Original Assignee
Rotam Agrochem International Co. Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rotam Agrochem International Co. Ltd filed Critical Rotam Agrochem International Co. Ltd
Priority to CN201480021741.6A priority Critical patent/CN105120668B/zh
Priority to AU2014264173A priority patent/AU2014264173B2/en
Publication of WO2014180215A1 publication Critical patent/WO2014180215A1/fr
Priority to AU2017100044A priority patent/AU2017100044A4/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • the present invention relates to an agrochemical composition, in particular to a nematicidal composition.
  • the present invention also relate to a method for preparing the said agrochemical composition and to its use in controlling nematodes.
  • Nematodes are microscopic round worms. They can generally be described as aquatic, triploblastic, unsegmented, bilaterally symmetrical roundworms, which are colourless, transparent, usually bisexual, and worm-shaped (vermiform), although some can become swollen (pyroform). It has been suggested that nematodes are the most abundant form of animal life and that to date only about 3% of nematode species have been studied in detail.
  • Plant parasitic nematodes typically feed on the roots or shoots of plants.
  • the nematodes can be ectoparasites, that is feeding on the exterior of a host plant, or endoparasites, that is living/feeding inside the host plant.
  • Parasitic nematodes can be migratory or sedentary. They constitute severe plant production constraints in many agronomic and horticultural crops. Severe infestations of endoparasitic nematodes, such as certain root-knot or cyst nematodes, can result in yield losses of from 10% to 50%. Worldwide crop losses due to plant parasitic nematodes have been estimated at $80 billion annually.
  • Some of the most commercially significant plant parasitic nematodes are: Meloidogyne; Root-knot nematode Pratylenchus; Lesion nematode Heterodera; Cyst nematode Globodera; Cyst nematode
  • Tylenchulus Citrus nematode Xiphinema; Dagger nematode
  • Nematodes are a serious pest and methods to control their parasitic activities are an important feature in maximising crop production in modern intensive agriculture.
  • Current pest management options for controlling nematodes are very limited.
  • Soil fumigants and effective non-fumigant nematicides, especially carbamate and organophosphate compounds, are increasingly under regulatory pressure because of potential undesirable effects on users, consumers, and the environment.
  • Other effective methods to reduce plant-parasitic nematode populations such as exposing infested soil to heat by steam treatment, are technically difficult and too costly for general or widespread application in the field.
  • Certain seed treatments for example using abamectin as a nematicide, have been shown to effectively protect roots of young seedlings against various plant pests, including plant-parasitic nematodes.
  • Non-protected root systems show stunting, and in the case of root-knot nematodes (Meloidogyne spp.) show more severe galling, in comparison to abamectin-protected plants.
  • These below-ground differences are reflected in significant height and dry weight differences of the shoots.
  • seed treatment protection against nematode invasion often lasts for only a relatively short period of time.
  • an improved agrochemical composition can be prepared from a combination of iprodione and at least one macrolide compound.
  • the present invention provides an agrochemical composition
  • iprodione and at least one macrolide compound selected from compounds of the general formula (I):
  • R h R 2 , R 3 , R 4 , R5 and R 6 independently represent hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyi, aryl or heterocyclyl group; and substructures A and B independently denote that the two carbon atoms to which each of these substructures is bonded are linked by a single bond, by a double bond or by a single bond and an epoxy bridge; and compounds of the general formula (II):
  • Ri2 is an alkyl, alkenyl or phenyl group
  • R 13 is OH
  • the combination of iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) provide a synergistic effect and improved control of nematodes and other plant pests and pathogens.
  • the combination exhibits surprisingly high activity in controlling nematodes in crops, such as tomato, pepper, cucumber, melons, coffee and soybeans.
  • synergistic as used herein is not to be understood in this connection as being restricted to the pesticidal activity of the combination, but also refers to other advantageous properties, compared with iprodione and the macrolide compounds applied individually.
  • advantageous properties which may be mentioned are: extension of the pesticidal spectrum of action to other pests, for example to resistant strains; reduction in the application rate of the macrolide compound, or control of the target pests with the aid of the compositions according to the invention at an application rate of iprodione and the macrolide compound alone that is ineffective; enhanced crop safety; improved quality of produce, such as higher content of nutrient or oil, better fiber quality, enhanced shelf life, reduced content of toxic products, for example such as mycotoxins, reduced content of residues or unfavorable constituents of any kind or better digestability; improved tolerance to unfavorable temperatures, draughts or salt content of water; enhanced assimilation rates, such as nutrient uptake, water uptake and photosynthesis; favorable
  • the agrochemical composition of the present invention is advantageous for controlling nematodes and other plant pests and pathogens, including such pests as Meloidogyne incognita and Meloidogyne javanica, in crops, such as tomato, pepper, cucumber, melons, coffee and soybeans.
  • the composition of the present invention comprises iprodione.
  • Iprodione is the common name for the compound 3-(3,5-dichlorophenyl)-N-isopropyl-2,4- dioxoimidazolidine-1 -carboxamide. Iprodione was first disclosed in US 3,755,350 as a fungicide, in particular for the control of dollar spot, brown patch, and leaf spot diseases in bentgrass.
  • composition of the present invention further comprises a macrolide selected from the compounds of general formulae (I) and (II), as set out above.
  • the macrolide compounds of formulae (I) and (II) are known in the art.
  • the macrolides are the classes of substances which are known as milbemycins and avermectins, and disclosed, for example, in US 4,310,519, US 5,077,298, DE 2 717 040 and US 4,427,663.
  • Ri is preferably hydrogen or a lower alkyl group, more preferably having from 1 to 4 carbon atoms, still more preferably methyl.
  • R 2 is preferably a heterocyclyl group, more preferably a group of the general formula (VI):
  • R 15 is a lower alkyl group, preferably having from 1 to 4 carbon atoms, in particular methyl or ethyl.
  • R 3 is most preferably hydrogen.
  • R 4 is preferably lower alkyl, more preferably having from 1 to 3 carbon atoms, in particular methyl.
  • R 5 is preferably a heterocycle group, more preferably the group of formula (VII):
  • R 6 is preferably a lower alkyl group, more preferably having from 1 to 3 carbon atoms, particular ethyl.
  • a and B are each preferably single or a double bond.
  • Preferred compounds of general formula (I) are spinosad and spinetoram.
  • Ri 2 is preferably an alkyl group having from 1 to 8 carbon atoms, more preferably from 1 to 6 carbon atoms, still more preferably from 1 to 4 carbon atoms.
  • the alkyl group may be straight chain or branched, preferably straight chain.
  • Preferred alkyl groups are methyl, ethyl, propyl and butyl.
  • R 12 is an alkenyl group, preferably having from 2 to 10 carbon atoms, more preferably from 2 to 8 carbon atoms, still more preferably from 2 to 4 carbon atoms.
  • the alkenyl group may be straight chain or branched, preferably branched.
  • a branched C 6 alkenyl group is preferred.
  • R 12 is preferably a phenyl group.
  • Preferred macrolide compounds of general formula (II) are ivermectin, abamectin, milbemectin, moxidectin, eprinomectin, lepimectin, selamectin and doramectin.
  • the macrolide compounds of general formulae (I) and (II) may be employed in its free form or in the form of a salt.
  • the agrochemically compatible salts of the macrolide compounds are, for example, acid addition salts of inorganic and organic acids, in particular of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, formic acid, acetic acid, tri-fluoroacetic acid, oxalic acid, malonic acid, toluenesulfonic acid or benzoic acid.
  • Abamectin is one preferred macrolide compound for use in the composition of the present invention.
  • Abamectin is a mixture of avermectin B 1a and avermectin B 1 b and is described, for example, in The Pesticide Manual, l OthEd. (1994), The British Crop Protection Council, London, page 3.
  • Abamectin is a commercially available compound.
  • emamectin that is 4"-De-oxy-4"-epi-N- methylamino avermectin B 1 b /B 1a , known from US 4,874,749.
  • Emamectin is also known as MK-244 and is described in Journal of Organic Chemistry, Vol. 59 (1994), pages 7704- 7708.
  • Agrochemically especially useful salts of emamectin are described in US 5,288,710.
  • a further preferred macrolide compound is the group of compounds consisting of the spinosyns and their derivatives; the group of compounds consisting of the naturally occurring spinosyns; and the group of compounds consisting of the derivatives of the naturally occurring spinosyns.
  • the active ingredient comprises spinosyn A, spinosyn D, or a mixture of spinosyn A and spinosyn D.
  • An especially component is spinosad. Spinosad is known from the "The Pesticide Manual", 1 1 th Ed. (1997), The British Crop Protection Council, London, United Kingdom, pages 1272-1273.
  • Preferred embodiments of the present invention are a composition which comprises, as the macrolide active ingredient, abamectin or spinosad, in particular in the free form, or emamectin, in particular as a salt, especially the benzoate salt.
  • Iprodione may be present in the composition in any suitable amount. In some embodiments of the invention, iprodione is present in an amount of 1 % to 99% by weight, preferably 30% to 90%, more preferably 50% to 80%.
  • the macrolide compounds of general formulae (I) and (II) may be present in the composition in any suitable amount.
  • the macrolide compound selected from the compounds of general formulae (I) and (II) is present in an amount of 1 % to 50% by weight, preferably 5% to 40%, more preferably 10% to 30%.
  • the composition may comprise a single macrolide compound selected from the compounds of general formulae (I) and (II). Alternatively, the composition may comprise a mixture of two or more macrolide compounds of formulae (I) and (II).
  • the weight ratio of iprodione and the macrolide compounds selected from the compounds of general formulae (I) and (II) may be in the range of from 1 :100 to 100:1 , preferably from 1 :50 to 50:1 .
  • the agrochemical composition of the present invention may further contain one or more agriculturally acceptable auxiliaries.
  • auxiliaries employed in the composition and their amounts will depend upon the type of formulation and/or the manner in which the formulation is to be applied by the end user.
  • Suitable auxiliaries are customary formulation adjuvant or components, such as solvents, surfactants, stabilizers, anti- foaming agents, anti-freezing agents, preservatives, antioxidants, colorants, thickeners and inert fillers.
  • auxiliaries are known in the art and are commercially available. Their use in the formulation of the compositions of the present invention will be apparent to the person skilled in the art.
  • the composition may comprise one or more solvents.
  • the solvent may be organic or inorganic. Suitable solvents are selected from customary solvents which thoroughly dissolve the agrochemically active substances employed. Suitable solvents are known in the art and are commercially available. Examples of suitable solvents include water; aromatic solvents, such as xylene (for example solvent products commercially available from SolvessoTM); mineral oils; animal oils; vegetable oils; alcohols, for example methanol, butanol, pentanol, and benzyl alcohol; ketones, for example cyclohexanone, and gamma-butyrolactone; pyrrolidones, such as NMP, and NOP; acetates, such as glycol diacetate; glycols; fatty acid dimethylamides; fatty acids; and fatty acid esters.
  • aromatic solvents such as xylene (for example solvent products commercially available from SolvessoTM)
  • mineral oils such as xylene (for example solvent products commercially available from So
  • the composition optionally further comprises one or more surfactants.
  • Suitable surfactants include, but are not limited to, alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, arylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl poly
  • composition optionally further comprises one or more polymeric stabilizers.
  • Suitable polymeric stabilizers that may be used in the present invention include, but are not limited to, polypropylene, polyisobutylene, polyisoprene, copolymers of monoolefins and diolefins, polyacrylates, polystyrene, polyvinyl acetate, polyurethanes or polyamides. Suitable stabilizers are known in the art and are commercially available.
  • the composition may include an anti-foaming agent.
  • Suitable anti-foam agents include those substances which can normally be used for this purpose in agrochemical compositions and will be readily apparent to the person skilled in the art.
  • Suitable anti- foam agents are known in the art and are commercially available.
  • Particularly preferred antifoam agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone anti-foam agents (for example commercially available from GE or Compton).
  • One or more preservatives may also be present in the composition. Suitable preservatives include those substances which can normally be used for this purpose in agrochemical compositions of this type and again are well known in the art. Suitable examples that may be mentioned include Preventol® (commercially available from Bayer AG) and Proxel® (commercially available from Bayer AG).
  • the composition may include one or more antioxidants. Suitable antioxidants are substances which can normally be used for this purpose in agrochemical compositions, as is known in the art. Preference is given, for example, to butylated hydroxytoluene.
  • the compositions may further comprise one or more solid adherents. Such adherents are known in the art and available commercially. They include organic adhesives, including tackifiers, such as celluloses of substituted celluloses, natural and synthetic polymers in the form of powders, granules, or lattices, and inorganic adhesives such as gypsum, silica, or cement.
  • the compositions may further comprise one or more inert fillers.
  • Suitable fillers include, for example, natural ground minerals, such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates.
  • natural ground minerals such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth
  • synthetic ground minerals such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates.
  • Suitable inert fillers for granules include, for example, crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, and dolomite, or synthetic granules of inorganic and organic ground materials, as well as granules of organic material, such as sawdust, coconut husks, corn cobs, and tobacco stalks.
  • compositions may further comprise one or more thickeners.
  • suitable thickeners include those substances which can normally be used for this purpose in agrochemical compositions.
  • suitable thickeners include gums, such as xanthan gum, PVOH, cellulose and its derivatives, clay hydrated silicates, magnesium aluminum silicates or a mixture thereof. Again, such thickeners are known in the art and are available commercially.
  • the agrochemical composition may be applied and used in pure form, or more preferably together with at least one of the auxiliaries, as described hereinabove.
  • composition of the present invention may also comprise other active ingredients for achieving specific effects, for example, bactericides, fungicides, insecticides, nematicides, molluscicides or herbicides. Suitable compounds for providing the aforementioned activities are known in the art and are commercially available.
  • the agrochemical composition of the present invention may be formulated in different ways, depending upon the circumstances of its use. Suitable formulation techniques are known in the art and include water-dispersible powders, dusts, pastes, water-dispersible granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates, suspoemulsion, aerosols, or microencapsulation suspensions. More preferably, the agrochemical composition is formulated as water-dispersible granules, an emulsifiable concentrate, a suspension concentrate, a suspoemulsion, or a microencapsulation suspension.
  • formulation types for use in the present invention are as follows:
  • Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are dissolved in a water-soluble solvent.
  • One or more wetting agents and/or other auxiliaries may be included.
  • the active compound dissolves upon dilution with water.
  • Emulsifiable concentrates Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are dissolved in a water-immiscible solvent, preferably with the addition of one or more non-anionic emulsifiers and anionic emulsifiers. The mixture is agitated, for example by stirring, to get a uniform formulation. Dilution with water provides a stable emulsion.
  • Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are dissolved in one or more suitable water immiscible solvents, preferably with the addition of one or more non-anionic emulsifiers and anionic emulsifiers.
  • the resulting mixture is introduced into water by appropriate means, such as an emulsifying machine, to provide a homogeneous emulsion. Dilution with water gives a stable emulsion.
  • iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are comminuted, preferably with the addition of one or more dispersants and wetting agents, and water or solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
  • Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are ground finely, preferably with the addition of one or more dispersants and wetting agents, and prepared as water-dispersible or water-soluble granules by means of suitable techniques, for example by extrusion, drying in a spray tower, or by processing in a fluidized bed. Dilution with water gives a stable dispersion or solution of the active compound.
  • Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are ground in a suitable apparatus, such as a rotor-stator mill, preferably with addition of one or more dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
  • Granules (GR, FG, GG, MG) Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are finely ground in a suitable apparatus, with addition of up to 99.5 parts by weight of carriers. Granules are then prepared either by suitable techniques, such as extrusion, spray-drying or using a fluidized bed.
  • the present invention provides the use of a composition as hereinbefore described in the control of pests at a locus, in particular for use as a nematicide.
  • the present invention provides a method for controlling pests, in particular nematodes, at a locus, comprising applying to the locus a composition as hereinbefore described.
  • composition of the present invention may be applied to the target plant or plant of interest, to one or more parts thereof (such as leaves or seeds), or to the locus thereof.
  • the present invention provides a method of controlling nematodes and other plant pests and pathogens at a locus, comprising applying to the locus iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II).
  • the aforementioned active compounds may be applied separately, for example simultaneously or consecutively, to the locus.
  • the active compounds are applied together, preferably in the form of a composition as hereinbefore described.
  • nematodes selected from the group consisting of root-knot, cyst, burrowing, dagger, lance, pin, reniform, lesion, ring, spiral, sting, stubby, stunt, stem and bulb, seed gall and foliar nematodes;
  • Paratrichodorus minor Longidorus spp., Helicotylenchus pseudorobustus, Hoplolaimus galeatus, H. columbus, H. tylenchiformis, Trichodorus proximus, Xiphinema index, X. americanum, Ditylenchus dipsaci, D. destructor, Nacobbus aberrans, Longidorus breviannulatus, L. africanus, Mesocriconema xenoplax, Aphelenchoides besseyi, A. fragariae, Zygotylenchus guevarai, Belonolaimus longicaudatus, B.
  • Globodera spp. for example G. rostochiensis, and G. pallida; Longidorus spp.;
  • Meloidogyne spp. for example Meloidogyne incognita and Meloidogyne javanica;
  • Pratylenchus for example P. neglectans, P. scribneri, P. thornei, P. brachyurus, P. coffeae, P. zeae, and P. penetrans
  • Radopholus spp. for example Radopholus similis, and R. citrophilus
  • Trichodorus spp. Trichodorus spp.
  • Tylenchulus for example Tylenchulus semipenetrans
  • Xiphinema spp. Trichodorus spp.
  • Tylenchulus for example Tylenchulus semipenetrans
  • Xiphinema spp. Xiphinema spp.
  • Heterodera spp. for example H. schachtii, H. avenae, H. glycines, H. ' carotae, H. goettingiana, H. zeae and H. trifolii; and
  • M. incognita M. javanica, M. hapla, M. arenaria, M. chitwoodi, M. graminis, M. mayaguensis, M. fallax, M. naasi.
  • Anoplura for example Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;
  • Heteroptera for example Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp. Eurygaster spp. Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Triatoma spp.; from the order Homoptera, for example Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella aurantii, Aphididae, Aphiscraccivora, A. fabae, A.
  • Homoptera for example Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella aurantii, Aphididae, Aphiscraccivora, A. fabae, A.
  • Hymenoptera for example Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;
  • Aedes spp. Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Taban
  • Siphonaptera for example Ceratophyllus spp. and Xenopsylla cheopis
  • Thysanura for example Lepisma saccharina and
  • Acarina for example Acarus siro, Aceria sheldoni; Aculus spp., especially A. Louendali; Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., especially B. californicus and B. phoenicis; Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., especially E.carpini and E. orientalis; Eriophyes spp., especially E.
  • Suitable target crops include, in particular, cereals, such as wheat, barley, rye, oats, rice, maize, sorghum, millet and manioc; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries and blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumbers and melons; fibrous plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus
  • the composition may be prepared and applied such that the agrochemical composition of iprodione and the macrolide compounds of formulae (I) and (II) are applied at any suitable rate, as demanded by the locus to be treated.
  • the application rate may vary within wide ranges and depends upon such factors as the soil constitution, the type of application (foliar application; seed dressing; application in the seed furrow), the target crop plant, the nematodes to be controlled, the climatic circumstances prevailing in each case, and other factors determined by the type of application, timing of application and target crop.
  • the application rates are from 1 to about 2000 g of the agrochemical composition per hectare, in particular 10 to 1000 g/ha, preferably 10 to 500 g/ha, more preferably 10 to 200 g/ha.
  • the iprodione and the macrolide active compounds of general formulae (I) and (II) may be applied in any suitable form, as described above, and applied to the locus where control is desired either simultaneously or in succession at short intervals, for example on the same day.
  • iprodione and the macrolide compound of general formulae (I) and (II) are applied simultaneously, in particular by way of a composition of the present invention.
  • Iprodione and the macrolide compounds of general formulae (I) and (II) may be applied to the plant or locus in any order.
  • Each compound may be applied just once or a plurality of times.
  • each of the compounds is applied a plurality of times, in particular from 2 to 5 times, more preferably 3 times.
  • the active compounds may be applied at any suitable time.
  • the active compounds are applied to the soil or the locus of the plant prior to planting, during planting, or after planting. Such a treatment may take place by conventional methods known in the art, for instance, drip-irrigation, spray, and soil fumigation.
  • the active compounds are applied to the plant propagation material, such as a seed, by seed coating. These application methods and corresponding application machines are known in the art.
  • Iprodione and the macrolide compounds of general formulae (I) and (II) may be applied in any amounts relative to each other.
  • the relative amounts of the compounds to be applied to the plant or locus are as hereinbefore described, with the ratio of iprodione and the macrolide compounds of general formulae (I) and (II) preferably being in the range of from 1 :100 to 100:1 .
  • iprodione and the macrolide compounds of general formulae (I) and (II) are applied simultaneously, they can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), optionally with other pesticides, or they can be obtained as a single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product)), and optionally mixed together with other pesticides.
  • a tank-mix, ready-to-apply, spray broth, or slurry optionally with other pesticides
  • a single formulation mixture source known as a pre-mix, concentrate, formulated compound (or product)
  • a water-soluble concentrate formulation was prepared having the following composition:
  • TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g
  • An emulsifiable concentrate was prepared having the following composition:
  • TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g
  • Example 3 Water-dispersible powders (WP) A water dispersible powder was prepared having the following composition:
  • Dispersogen1494 sodium salt of a cresol-formaldehyde 5 g condensation
  • a water dispersible granule formulation was prepared having the following composition:
  • Dispersogen1494 sodium salt of a cresol-formaldehyde 5 g condensation
  • a suspension formulation was prepared having the following composition: Iprodione 2 g
  • Dispersogen 4387 anionic polymeric ester 5 g
  • a water soluble concentrate was prepared having the following composition:
  • TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g
  • a water dispersible granule was prepared having the following composition: Iprodione 16 g
  • Dispersogen 1494 sodium salt of a cresol-formaldehyde 5 g condensation
  • a flowable seed treatment was prepared having the following composition:
  • Dispersogen 4387 anionic polymeric ester 5 g
  • a water soluble concentrate was prepared having the following composition: Iprodione 25 g
  • TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g
  • Example 10 Water-dispersible granule (WG) A water-dispersible granule formulation was prepared having the following composition:
  • Dispersogen 1494 sodium salt of a cresol-formaldehyde 5 g condensation
  • Example 1 Oil-in-water emulsion (EW)
  • An oil-in-water emulsion formulation was prepared having the following composition: Iprodione 8 g Abamectin 4 g Solvesso 200 20 g
  • a suspension formulation was prepared having the following composition:
  • Dispersogen 4387 anionic polymeric ester 5 g
  • Test 1 Nematicidal activity against Meloidogyne incognita
  • 100 Meloidogyne incognita was introduced uniformly. Three replicates of each treatment were tested. Iprodione (Rovral® from Bayer), abamectin (Agador® from Syngenta), emamectin benzoate (Affirm® from Syngenta), spinosad (Success from Dow) and formulations of each of Examples 1 to 12 set out above were applied. Efficacy was assessed based on mortality rate after 24 and 48 hours. The results are set out in the table below.
  • the formulations prepared according to the present invention exhibited significantly improved efficacy in controlling the target pests than the commercially available compositions.
  • Test 2 Nematicidal activity against Meloidogyne javanica
  • Test 1 The general procedure of Test 1 was repeated to assess the nematicidal activity against Meloidogyne javanica.
  • the formulations prepared according to the present invention exhibited significantly improved efficacy in controlling the target pests than the commercially available compositions.
  • the formulations prepared according to the present invention exhibited significantly improved efficacy in controlling the target pests than the commercially available compositions.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition agrochimique comprenant de l'iprodione et au moins un composé de macrolide sélectionné dans les composés représentés par la formule (I). Dans cette formule, R1, R2, R3, R4, R5 et R6 représentent indépendamment hydrogène ou alkyle substitué ou non substitué, alcényle, alcynyle, cycloalkyle, aryle ou un groupe hétérocyclique ; les sous-structures A et B démontrent indépendamment que les deux atomes de carbone auxquels chacune d'elles est liée, sont liées par une liaison simple, une liaison double, une liaison simple et un pont époxy. L'invention concerne également des composés représentés par la formule (II), dans laquelle R7 représente hydrogène ; R8 représente hydrogène ou un groupe de la formule (III) dans laquelle R9 représente OH ou CH3-CO-NH- ; dans le groupe de la formule (IV) ou le groupe de la formule (V), D représente une liaison simple, auquel cas R10 et R11 représentent à la fois hydrogène ou sont combinés afin de former le groupe =N-O-CH3 ou D représente une liaison double et R10 et R11 sont combinés pour représenter hydrogène ; R12 représente un groupe alkyle, alcényle ou phényle ; et R13 représente OH, R14 représente hydrogène ou R13 et R14 sont combinés pour former le groupe =N-OH. La composition est utilisée pour lutter contre les organismes nuisibles sur un lieu, en particulier les nématodes.
PCT/CN2014/075131 2013-05-07 2014-04-11 Composition agrochimique et son procédé de préparation et d'utilisation WO2014180215A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201480021741.6A CN105120668B (zh) 2013-05-07 2014-04-11 农用化学品组合物、其制备方法及其用途
AU2014264173A AU2014264173B2 (en) 2013-05-07 2014-04-11 Agrochemical composition, method for its preparation and use thereof
AU2017100044A AU2017100044A4 (en) 2013-05-07 2017-01-12 Agrochemical composition, method for its preparation and the use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1308136.9 2013-05-07
GB1308136.9A GB2513859B (en) 2013-05-07 2013-05-07 Agrochemical composition, method for its preparation and the use thereof

Publications (1)

Publication Number Publication Date
WO2014180215A1 true WO2014180215A1 (fr) 2014-11-13

Family

ID=48627355

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2014/075131 WO2014180215A1 (fr) 2013-05-07 2014-04-11 Composition agrochimique et son procédé de préparation et d'utilisation

Country Status (5)

Country Link
CN (1) CN105120668B (fr)
AU (2) AU2014264173B2 (fr)
GB (1) GB2513859B (fr)
TW (1) TWI646894B (fr)
WO (1) WO2014180215A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105557728B (zh) * 2014-10-10 2017-09-19 四川利尔作物科学有限公司 农药组合物及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1941798A2 (fr) * 2004-12-17 2008-07-09 Devgen NV Compositions nematicides
CN101669517A (zh) * 2009-10-13 2010-03-17 深圳诺普信农化股份有限公司 一种杀线虫组合物
CN102271512A (zh) * 2008-12-29 2011-12-07 拜耳作物科学公司 用苯基吡唑类和氯化烟酰类的混合物处理转基因作物
CN102960359A (zh) * 2012-11-26 2013-03-13 海南正业中农高科股份有限公司 二硫氰基甲烷与大环内酯类杀虫成分的组合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0076580B1 (fr) * 1981-10-06 1986-09-10 Imperial Chemical Industries Plc Procédé pour combattre les pestes nématodes de plantes et compositions pour cela
GB0118137D0 (en) * 2001-07-25 2001-09-19 Syngenta Ltd Insecticidal mixture
TWI381811B (zh) * 2006-06-23 2013-01-11 Dow Agrosciences Llc 用以防治可抵抗一般殺蟲劑之昆蟲的方法
CN101019509B (zh) * 2007-03-30 2010-08-11 大连佛伦德球根花卉有限公司 东方百合鳞片籽球的工厂化生产方法
CN101946668A (zh) * 2010-08-13 2011-01-19 刘秀秀 一种果树的夏季管理应用方法
ES2625504T3 (es) * 2011-05-03 2017-07-19 Dow Agrosciences Llc Integración de genes en el cromosoma de Saccharopolyspora spinosa
CN102885033A (zh) * 2012-09-28 2013-01-23 王龙华 一种水乳剂杀虫剂及其生产工艺

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1941798A2 (fr) * 2004-12-17 2008-07-09 Devgen NV Compositions nematicides
CN102271512A (zh) * 2008-12-29 2011-12-07 拜耳作物科学公司 用苯基吡唑类和氯化烟酰类的混合物处理转基因作物
CN101669517A (zh) * 2009-10-13 2010-03-17 深圳诺普信农化股份有限公司 一种杀线虫组合物
CN102960359A (zh) * 2012-11-26 2013-03-13 海南正业中农高科股份有限公司 二硫氰基甲烷与大环内酯类杀虫成分的组合物

Also Published As

Publication number Publication date
TWI646894B (zh) 2019-01-11
AU2017100044A4 (en) 2017-02-23
AU2014264173B2 (en) 2017-11-09
GB201308136D0 (en) 2013-06-12
CN105120668A (zh) 2015-12-02
GB2513859B (en) 2018-01-17
CN105120668B (zh) 2018-05-04
AU2014264173A1 (en) 2015-11-05
GB2513859A (en) 2014-11-12
TW201446142A (zh) 2014-12-16

Similar Documents

Publication Publication Date Title
RU2447660C2 (ru) Пестицидные комбинации и способ борьбы с сельскохозяйственными вредителями растений
CN100527958C (zh) 大环内酯在害虫防治中的应用
US20030232764A1 (en) Use of macrolides in pest control
RU2369096C2 (ru) Способ защиты материала для размножения растений от нашествия насекомых
MX2007013722A (es) Composiciones pesticidas.
US8598130B2 (en) Insecticidal combinations
BRPI9917838B1 (pt) método de controle de pragas em culturas de planta transgênica útil que expressa uma endotoxina de bacillus thuringiensis cry ia(c)
US20130059730A1 (en) Insecticidal combination
JP4902081B2 (ja) ピロキロン化合物とネオニコチノイド化合物とからなる組成物
AU2017100044A4 (en) Agrochemical composition, method for its preparation and the use thereof
TW202005530A (zh) 新型農用化學組合
PT2077720E (pt) Composições pesticidas contendo um azol, uma fenilamida e azoxistrobina
WO2020044215A1 (fr) Nouvelles combinaisons insecticides
GB2550089A (en) Agrochemical composition, method for its preparation and the use thereof
AT502357B1 (de) Verfahren zum schutz von pflanzlichem vermehrungsgut und später zuwachsenden pflanzenteilen vor schädlingsbefall
CN101584328A (zh) 大环内酯在害虫防治中的应用
CH690561A5 (de) Mittel mit pestiziden und mikrobioziden Eigenschaften enthaltend ein Oxadiazol und einen fungizid aktiven Stoff.

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201480021741.6

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14794789

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2014264173

Country of ref document: AU

Date of ref document: 20140411

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14794789

Country of ref document: EP

Kind code of ref document: A1